Pilot Will is more interested in finding the perfect gift for his son Nathan's 13th birthday than in doing his job selling insurance. His best friend, sensitive soul Craig, still pines for his college ex, Lisa. Will's brother-in-law, Kenny, clamps down on his anger and asks himself, "What would Tobey Maguire do?," when his ex-wife, Brenda, starts seeing a guy who is everything he's not and much better looking. After Craig crashes Lisa's wedding to try to win her back, they are all faced with an opportunity to "man up" and be like their forefathers.
Finessing The Bromance Kenny gets jealous when Will and Grant strike up an unlikely "bromance." Things go from bad to worse when he finds out Grant is coming to the weekly Keen Sunday dinner. In an attempt to strike some common ground, the guys try a "Star Wars" screening, a film Kenny is obsessed with, but Grant has never seen.
Digging Deeper Roommates Kenny and Craig decide to dig a swimming pool after Will suggests that they do something together. And Theresa wants Will to take a class with her so they can spend more time together. But Brenda thinks she's spending too much time with Grant.
Wingmen When Kenny admits he hasn't had a date since his divorce from Brenda - and that Brenda is the only woman he has ever slept with - the guys, including Grant, take him clubbing to jump start his love life. But things don't go as planned, especially when a friend of Theresa's sees Will and thinks he's stepping out on his wife.
Acceptance As a rite of passage, Will decides to buy his son, Nathan, a cell phone, which in turn gives Brenda the idea to also purchase one for Grant to upgrade his old brick phone. Kenny is nervous about meeting his new girlfriend Jane's parents, and as expected, when he finds out her parents are lesbians and also therapists, the situation goes from bad to worse. Her parents also own a coffee shop and end up giving Craig a music gig there, only to see the nice gesture backfire when he gets the wrong idea about the coffeehouse manager. Meanwhile, Theresa installs a tracking device on Will's cell phone, which he fears will lead to her finding out about the secret Dad's club he sometimes attends after work.
High Road Is The Guy Road Will struggles to take the high road after a kid at school starts bullying Nathan, especially after Theresa tells him the kid's mom is on the school board, which Theresa is lobbying for funding for the science club. But when he learns that the kid's dad is Dennis Mayder, the same guy who mercilessly bullied Will and the gang back in the day, he looks to his friends - and Grant - for help.
Disciplining The Keens After they find out that Nathan's allergic, the whole family goes on a gluten free diet, which leads to a weird competition between Will and Theresa to see who can keep the diet up longer, and for Brenda, who's trying to convince health-conscious Grant she can live without it. Problem is, they're all cheating. Meanwhile, it's all fast food, all the time for Craig and Kenny as they romance two ladies who work at Big Burger.
Men And Their Chickens Will hopes that adopting a baby chick for little Lucy will be a "teachable moment" about where food comes from, but things get out of hand when all of the guys decide they want to adopt chicks too; Craig dates an attractive doctor, but finds himself intimidated by her bully of a son.
Fear Will installs a new home security system, but instead of making everyone feel safer, the system keeps tripping and wreaks havoc in all their lives. Meanwhile Craig reconnects with Lisa, the girl whose wedding he broke up; and Grant convinces Kenny to play a "trust the universe" game with him with his new GPS, letting the GPS randomly select their destination - Kenny is convinced it will eventually lead to disaster, but instead he and Grant end up on a series of wild adventures, which eventually finds Kenny meeting his "Star Wars" hero, Billy Dee Williams.